1-(4-Pyridyl)piperazine → HCID 18918505, compound

HRID 864798Notes

Reaction equation

HRID 864798 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10](Cl)[CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([OH:17])=[O:16])=[CH:4]1)[CH3:2].[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1>CO>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:27]3[CH2:28][CH2:29][N:24]([C:21]4[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=4)[CH2:25][CH2:26]3)[CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([OH:17])=[O:16])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 156185627-Chloro-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 18918505HCID 18918505, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 1-ethyl-7-chloro-4-quinolon-3-ylcarboxylic acid (182 mg) and 1-(4-pyridyl) piperazine (125 mg ) was heated to 200° C. for 20 minutes. The mixture was cooled and methanol (5 ml) was added. The resulting solid was filtered and washed with methanol (10 ml) to give the title compound (68 mg), as a solid: NMR (d6DMSO) δ1.4(t,3H), 3.75-3.85(m,4H), 3.9-4.0(m,4H), 4.55(q,2H), 6.9(d,1H), 7.2(d,2H), 7.3(dd,1H), 8.2(d,1H), 8.3(d,2H), 8.9(s,1H); m/e 379(M+H)+

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe resulting solid was filtered
  3. washwashed with methanol (10 ml)

Sources & evidence

ORD record
ord-f50520377a104fd49ff7dd920f548b35
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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